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According to the United States Census Bureau, the town has a total area of 15.6 square miles (40.4 km²), of which 11.7 square miles (30.3 km²) is land and 3.9 square miles (10.1 km²) (25.06%) is water.

In 1813, the village of Sing Sing was incorporated, and in 1845, the New York State Legislature created a new town out of the northern part of what had been the Town of Mount Pleasant. A local Indian authority suggested the town be named Ossinsing, a different form of the name Sing Sing. One year later the last "s" was removed for ease in pronunciation. In 1881, the town considered changing its name to "Garfield Plains" to honor the recently assassinated President of the United States, James Garfield, but dropped the idea after the much larger city of White Plains in southern Westchester County objected. In 1901, to prevent confusion of goods made in the village with Sing Sing prison-made items, local officials had the village name changed to Ossining as well.

In 1902 an area east of the village of Ossining, then known as Whitson's Crossing, was incorporated as the village of Briarcliff Manor.

There were 12,355 households out of which 33.1% had children under the age of 18 living with them, 54.4% were married couples living together, 10.7% had a female householder with no husband present, and 30.9% were non-families. 25.5% of all households were made up of individuals and 9.0% had someone living alone who was 65 years of age or older. The average household size was 2.64 and the average family size was 3.14.

In the town the population was spread out with 21.8% under the age of 18, 7.8% from 18 to 24, 34.5% from 25 to 44, 22.9% from 45 to 64, and 13.0% who were 65 years of age or older. The median age was 37 years. For every 100 females there were 106.1 males. For every 100 females age 18 and over, there were 105.4 males.

The median income for a household in the town was $65,485, and the median income for a family was $81,943 (these figures had risen to $77,753 and $98,593 respectively as of a 2007 estimate[4]). Males had a median income of $51,286 versus $40,618 for females. The per capita income for the town was $34,195. About 5.0% of families and 8.4% of the population were below the poverty line, including 8.3% of those under age 18 and 9.2% of those age 65 or over.

Ossining is ranked the #2 best community to live in Westchester by Westchester Magazine, based on criteria such as Diversity, Housing Costs, Parks & Recreation, Property Tax, Proximity to NYC, Safety, Schools, Proximity to Water, Nightlife, Shopping, and Downtown.

The Town of Ossining is governed by a town supervisor and a 4 member town board. The two incorporated villages of Ossining and Briarcliff Manor each have a mayor and a village board. Each village maintains its own police department and village justice court. In addition to the two incorporated villages there is an unincorporated section of the town that is not part of either village. The unincorporated section of the town has its own highway department. Fire, EMS and water services are provided by either Ossining Village or Briarcliff Manor. Law enforcement services for the unincorporated section of the town are provided through an inter-municipal agreement with the Village of Ossining Police Department (The town's police department was disbanded in 2011).

The Ossining Public Library, originally chartered in 1893 as the Sing Sing Public Library, serves the residents of the Ossining School District which includes the Village and Town of Ossining, and parts of Briarcliff Manor, Yorktown, and New Castle. The current collections of the library include over 110,000 books, 25,000 non-print items, and 300 newspaper and magazine titles. As a charter member of the 38-member Westchester Library System, the Ossining Public Library can also offer its patrons access to the more than one million holdings of the other county libraries. An ambitious ($15.8 million) building program was started in 2005 to replace its 1960s-era facility with a new 48,000-square-foot (4,500 m2) building. The new Ossining Public Library opened in March, 2007 and added many new or enhanced services, including over 50 public Internet terminals, a 250-seat theater, an art gallery, a cafe, and the county's first radio frequency (RFID) circulation system.[5]